Solopreneur Survival Guide - The 5 Hardest Things About Working Alone & How to Conquer Them

Being your own boss comes with some pretty awesome benefits. You can set your own hours, be selective about your projects, take working vacations — and even work in your PJs, should you choose! Despite the amazing advantages that come with customizing your professional life, a third of Americans want to be their own boss, yet never get past “the dreaming stage." In many ways, this is a shame, since their many talents will never be discovered.

If you've always dreamed of being a solopreneur, don't let yourself fall into becoming one of these statistics. Instead, share your talents with the world. Lots of people understand this struggle and have found ways to overcome it. Here are five of the hardest things about working alone, and ways you can conquer these obstacles.

1. Fear of unreliable income

Many of the things holding people back are related to money. Not knowing when or how much your next paycheck will be can be daunting. This is definitely a realistic fear. However, if you go into solopreneurship with your eyes wide open and have a plan, you can mitigate any potential paycheck problems.

• Set aside money. Set yourself up with a nest egg before you quit your day job so you’ll have cash stashed to tide you over.
• Make more money. Create several streams of income to ensure you always have some money trickling in.
• Pursue startup money. With backing from investors or lenders, you can launch and run your business without breaking your personal bank.

If you give yourself a bit of financial buffer, it helps to melt fears of unreliable income away and can get you through any rough times.

2. Concerns about finding startup money

Speaking of startup money, one of the top issues holding many would-be solopreneurs back is not having the startup money to help their businesses. According to a 2018 survey, 42% said obtaining working capital was their primary obstacle. The good news is, there are several funding options.

• Try crowdfunding. Launch a campaign on a crowdfunding site. Kickstarter and GoFundMe are two very popular options. Just be sure to detail your project and keep your supporters updated. (Also, it’s nice to offer them some kind of reward in exchange for their support).
• Take out a loan. Many companies find success in taking out a small business loan to get themselves up and running.
• Explore angel investors. Angel investing is a good opportunity, but be sure to always understand the terms; some investors will want to have some say in managing your business. If you don’t want interference, this probably won’t be a good option for you.
• Consider venture capital. Venture capitalists will give startup money, but they usually want to take a little bit of equity in your business in exchange. Some may also want a managerial say, so be sure to weigh any terms and implications carefully.

Don’t throw in the towel too soon if finding startup money is your challenge. Funding is not always as hard as you think. Explore all the available options and see what you can work out.

3. Worries about messing up self-employment taxes

Taxes are daunting enough for individuals. But for business owners, there is even more detail to cover to be sure you’re filing your paperwork properly with Uncle Sam. To help overcome this obstacle, take advantage of technology – use expense-tracking apps and an online calculator to help you figure your tax expenses and deductions.

4. No one to turn to in times of need

Some entrepreneurs worry about shouldering all the responsibility and having no one to turn to in times of adversity. And it’s true: When you fly solo in business, you’re ultimately where the buck stops. However, that doesn’t mean you have to operate entirely alone.

• Get coaching. Find yourself an executive coach to teach you the tricks of your trade and provide a safe space to share burdens and identify solutions.
• Use “training wheels.” Connect with a mentor who can help guide you through the rough stuff until you get a handle on how to anticipate problems and create solutions.
• Join a group. Look into both online and offline networks in your industry. Get comfortable with asking questions and you’ll easily receive answers to questions you have.
• Rent a coworking space. When you work in the company of others, instead of being isolated, you’ll be able to discuss ideas and problems with others to get feedback.
• Attend networking events. You can learn a lot from putting yourself out there in the center of the action at a trade show or conference. Be sure to take along a trade show checklist so you know what you’re doing as you get started.

Essentially, you’ll want to set yourself up with a solid support system. Connection with others can offer you emotional encouragement as well as logistical advice and possibly resources. And remember to always be willing and ready to help others when they face their own challenges.

5. Fear of isolation

Isolation is rough, especially if you’ve never worked alone for long periods of time. If you’re a solopreneur living in a remote area, or one who doesn’t have much of an ability to connect with others, why not try relocating to a new city that offers more opportunities to make connections?

Growing cities like this are a great place to be if you’re looking to augment your business ventures, especially if they’re affordable and accessible. For instance, Kansas City has one of the country’s lowest costs of living but a burgeoning job market and accompanying opportunities.

While going out on your own is scary, the rewards are absolutely worth the risks. The best way to mitigate those risks is to meticulously do your homework, find solutions to anticipated problems before they happen, and be prepared overall. Once you’ve cleared the hurdles and are on your way to solo success, you can then reap the benefits and enjoy the excitement and satisfaction that comes with success.

Don’t just dream it! Take action and set yourself up to enjoy the solopreneur lifestyle you've always wanted.